|本期目录/Table of Contents|

[1]刘安昌,邓　三,李　琪,等.有机发光材料中间体1-羟基芘的合成工艺研究[J].武汉工程大学学报,2021,43(02):128-130.[doi:10.19843/j.cnki.CN42-1779/TQ.202011018]
　LIU Anchang,DENG San,LI Qi,et al.Synthesis of 1-Hydroxypyrene as Intermediate in Organic Light-Emitting Materials[J].Journal of Wuhan Institute of Technology,2021,43(02):128-130.[doi:10.19843/j.cnki.CN42-1779/TQ.202011018]
点击复制

有机发光材料中间体1-羟基芘的合成工艺研究(/HTML)
分享到：

《武汉工程大学学报》[ISSN:1674-2869/CN:42-1779/TQ]

卷:
43
期数:
2021年02期
页码:
128-130
栏目:
化学与化学工程
出版日期:
2021-04-30

文章信息/Info

Title:
Synthesis of 1-Hydroxypyrene as Intermediate in Organic Light-Emitting Materials
文章编号:
1674 - 2869（2021）02 - 0128 - 03
作者:
刘安昌; 邓　三; 李　琪; 何良莉; 李惠竹
武汉工程大学化工与制药学院，湖北 武汉 430205
Author(s):
LIU Anchang;  DENG San;  LI Qi ;  HE Liangli;  LI Huizhu
School of Chenmical Engineering and Pharmacy， Wuhan Institute of Technology Wuhan 430205， China
关键词:
有机发光材料; 1-羟基芘; 中间体合成
Keywords:
organic light-emitting materials; 1-hydroxypyren;  intermediate synthesis
分类号:
O625.29
DOI:
10.19843/j.cnki.CN42-1779/TQ.202011018
文献标志码:
A
摘要:
1-羟基芘是一种重要的有机电致光材料中间体，该中间体能与一些芳烃及其衍生物进一步反应得到不同性质的光电材料，具有广阔的市场前景。为获得1-羟基芘，本文以芘为原料，在二氯甲烷溶液中，在三氯化铝的催化下与乙酰氯反应得到1-乙酰芘；然后与间氯苯过甲酸或过氧硼酸发生bayer-villiger反应，得到1-乙酰氧基芘；接着在甲醇和四氢呋喃混合溶液中水解得到1-羟基芘，该合成路线短，原料易得，适应工业化生产，经1HNMR光谱鉴定，产物与1-羟基芘结构一致。
Abstract:
1-Hydroxypyrene is an important intermediate of organic electro-optical materials， which can react with some aromatic hydrocarbons and their derivatives to obtain optoelectronic materials with different properties. Thus， 1-hydroxypyrene has a broad market prospect. In order to obtain 1-hydroxypyrene， 1-acetyl pyrene was firstly obtained through the reaction of pyrene with acetyl chloride， catalyzed by aluminum chloride in dichloromethane solution. Then 1-acetyl pyrene reacted with m-chlorobenzeneperic acid or peroxyboric acid by bayer-villiger reaction to give 1-acetoxypyrene. Finally， 1-acetoxypyrene was hydrolyzed to give the target compound 1-hydroxypyrene in a mixed solution of methanol and tetrahydrofuran. The synthesis route presented is short with the easily available raw materials， thus it is suitable for industrial production. Identified by 1H nuclear magnetic resonance spectroscopy， the product is consistent with the 1-hydroxypyren.

参考文献/References:

［1］　韩爱英，赵晓宇，宋文志，等. 一种1-羟基芘及其中间体的合成方法：中国，105732331［P］. 2016-03-17.?

［2］　SCHERR J ， NEUHAUS A ， PAREY K ， et al. Noncovalent functionalization of carbon substrates with hydrogels improves structural analysis of vitrified proteins by electron cryo-microscopy［J］. ACS Nano ，2019， 13（6）：7185-7190.?
［3］　SIDERI I， VOUTYRITSA E. Green photoorgano-catalytic synthesis of phenols from arylboronic acids［J］. Synlett， 2017，29（10）：1324-1328.?
［4］　MAEDA H，AKAI T，SEGI M. Photo-fries rearrange-ment of 1-pyrenyl esters［J］. Tetrahedron Letters， 2017，58（46）：4377-4380.?
［5］　NELSEN D L， ANDING B J， SAWICKI J L， et al. Chromophore quench-Labeling： an Approach to quantifying catalyst speciation as demonstrated for （EBI）ZrMe2/B（C6F5）3-catalyzed polymerization of 1-hexene［J］. ACS Catalysis， 2016， 6（11）：7398-7408.?
［6］　BARABANOV I I， POLUKHIN A V ， KOROIEV V V， et al. Novel covalently linked pyrene-aryl azide systems： synthesis of 1-（4-azidobenzoyloxy）pyrene［J］. Mendeleev Communications， 2015， 25（4）：260-261.?
［7］　PASSARELL J V， FAIRFIELD D J， SATHER N A ， et al. Enhanced out-of-plane conductivity and photovoltaic performance in n = 1 layered perovskites through organic cation design［J］. Journal of the American Chemical Society， 2018， 140（23）：7313-7323.?
［8］　LIM G M. Method for the preparation of hydroxy aromatic polycyclic compound：KR，1661742［P］. 2016-09-30.?
［9］　GUESMI N E， HUSSEIN E M， AHMED S A， et al. Nucleophilicity and solvent effects on the kinetics of 4-（pyren-1-yl）thiazol-2-amine interaction with 4，6-dinitrobenzofuroxan［J］. Arabian Journal of Chemistry， 2020， 13（2）：3702-3713.?
［10］　朱红伟，姜杰，孙冰，等. 双氧水氧化工艺安全研究策略［J］. 无机盐工业，2021，53（1）：77-81.
?［11］　ASGHAR B H M， CRAMPTON M R . Rate-limiting proton-transfer in the sigma-adduct forming reactions of 1，3，5-trinitrobenzene and 4-nitrobenzofuroxan with substituted anilines in dimethyl sulfoxide. ［J］. Organic & Biomolecular Chemistry， 2005， 3（21）：3971-3978.?
［12］　GEORGE S R D， FRITH T D H， THOMAS D S， et al. Putting corannulene in its place. Reactivity studies comparing corannulene with other aromatic hydrocarbons［J］. Organic & Biomolecular Chemistry， 2015， 13（34）：9035-9041.?
［13］　FETZER J C. The chemistry and analysis of large pahs［J］. Polycyclic Aromatic Compounds， 2007， 27（2）：143-162.?
［14］　SEHGAL R K， KUMAR S . A simple preparation of 1-hydroxypyrene［J］. Organic Preparations and Procedures International， 1989， 21（2）：223-225. ［15］　CHEN L， PENG S， CHEN Y. Cooperative assembly of pyrene-functionalized donor/acceptor blend for ordered nanomorphology by intermolecular noncovalent π-π interactions. ［J］. ACS Applied Materials & Interfaces，2014，6（11）：8115-8123.?
［16］　PASSARELLI J V， FAIRFIELD D J， SATHER N A， et al. Enhanced out-of-plane conductivity and photovoltaic performance in n=1 layered perovskites through organic cation design［J］. Journal of the American Chemical Society， 2018， 140（23）：7313-7323.

相似文献/References:

[1]刘安昌,李　琪,邓　三,等.有机发光材料中间体5，10-二氢-5-苯基苯并［b］吲哚并［2，3-d］［1］苯并氮杂?的合成工[J].武汉工程大学学报,2021,43(03):256.[doi:10.19843/j.cnki.CN42-1779/TQ. 202011033]
　LIU Anchang,LI Qi,DENG San,et al.Synthesis of Organic Light-Emitting Materials Intermediate 5，10-Dihydro-5-Phenylbenz［b］Indolo［2，3-d］［1］Benzazepine[J].Journal of Wuhan Institute of Technology,2021,43(02):256.[doi:10.19843/j.cnki.CN42-1779/TQ. 202011033]

备注/Memo

备注/Memo:
收稿日期：2020-11-13作者简介：刘安昌，博士，教授。E-mail：[email protected]引文格式：刘安昌，邓三，李琪，等. 有机发光材料中间体1-羟基芘的合成工艺研究［J］. 武汉工程大学学报，2021，43（2）：128-130，138.
更新日期/Last Update: 2021-04-26